Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:23])[C:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=3[CH3:22])=[C:6]2[N:5]=[C:4]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:3]=1.C(N(C(C)C)CC)(C)C>C(O)C.O1CCOCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C.Cl.C([Mo](C=O)(C=O)(C=O)(C=O)C=O)=O.[Pd]>[CH3:23][C:9]1[C:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[C:13]=2[CH3:22])=[C:6]2[N:5]=[C:4]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:3]=[CH:2][N:7]2[N:8]=1To a suspension of 7-chloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-5-(tetrahydro-2H-pyran-4-yl)pyrazolo[1,5-a]pyrimidine (85 mg, 0.201 mmol) in ethanol (2 mL) and 1,4-dioxane (2 mL) were added hexaformylmolybdenum (27.1 mg, 0.100 mmol), Pd/C (1.0 mg, mmol) and DMAP (49 mg, 0.4 mmol) and diisopropylethylamine (26 mg, 0.2 mmol). The reaction mixture was irradiated (microwave) and stirred at 150° C. for 15 minutes. Reaction mixture was cooled down, diluted with ethyl acetate (30 mL) and 5% HCl solution. Two layers were separated. Organic layer was dried and concentrated to dryness. The crude product was purified to yield the titled compound (16 mg, 21%); LC/MS: MS (ES+) m/e 390 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.81 (m, 4H) 2.28 (s, 3H) 2.45-2.49 (m, 3H) 2.96 (s, 1H) 3.37-3.47 (m, 3H) 3.92 (br. s., 2H) 4.10 (s, 2H) 6.89 (d, J=7.33 Hz, 1H) 7.34 (s, 1H) 7.52 (s, 1H) 8.86 (d, J=7.33 Hz, 1H).
Wird geladen…